Sodium Carbonate → HCID 67260750, compound

HRID 2359101Notes

Reaction equation

HRID 2359101 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][CH3:9])=[CH:5][C:4]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[N:3]1.[I:15]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[I:15][C:5]1[C:4]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[N:3][N:2]([CH3:1])[C:6]=1[CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 67260613HCID 67260613, compound

Product 1

HCID 67260750HCID 67260750, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-methyl-5-propyl-3-(2-thienyl)-1H-pyrazole (2.5 mmol) in 7 mL dry N,N-dimethylformamide under argon atmosphere was added N-iodosuccinimide (2.6 mmol) in small portions at 0° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. 5% aqueous sodium thiosulfate solution and saturated aqueous sodium carbonate solution were added and the mixture was stirred at room temperature for 1 h, then extracted with MTBE. The combined organic extracts were successively washed with water and brine, dried over MgSO4, filtered and concentrated to afford 720 mg of 4-iodo-1-methyl-5-propyl-3-(2-thienyl)-1H-pyrazole (88% yield) that was used in the next step without further purification.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. extractionextracted with MTBE
  3. washThe combined organic extracts were successively washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8a693553ccd64832a93dfaecd79ff17a
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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